Best Questions To Ask On A First Date Or Online Dating

admin Samantha Jayne 3 Comments

Dating can be daunting even for the most confident person. So if you want to ease the nerves and create a genuine connection it’s important to be prepared. Just like if you were taking an exam you would study, know your material dating is very much the same. Preparation is key because you want things to feel natural rather than awkward silences or peppering a person with questions that feel like an interview.


So If You’d Like To Know The Best Questions To Ask On A First Date, Then Read On!

So let’s start with the online dating messages. Here are the best questions to ask when online dating that can dramatically boost your success.  Because you know that you never get a second chance to make an excellent first impression and that can mean the difference between getting offline faster or being stuck in the singles scene.

The very first message you send can be your only chance to capture a potential partner’s attention or quickly lose their interest.

A thoughtful question that sparks interest will get the conversation flowing and result in an exchange of details and face to face meeting.

Before I share, the Do’s let get the Don’ts on online dating message out of the way.

The Do’s And Don’t Of Online Dating Messages.

THE BIGGEST TABOO is the mistake most often made.

# 1 NEVER Send A Message that says,

“Hi,” “Hey” or “How are you” or “Hey, how’s it going?” or “How’s your day?”. This destroys attraction because it is entirely effortless and lacks interest and is purely annoying. In most cases, it is an absolute turn off; it is considered hard work because the person receiving it needs to think too much.
Think about it, how to do you tell someone you don’t know in a text or email how you are going in a text.

# 2 Never write Long Paragraphs or ask multiple questions.

It will seem like an essay, and they will lose interest. And multiple questions are so overwhelming.

# 3 Bad Spelling or Gramma.

You only get one first impression. If this is not your strength, there is a brilliant program called Grammarly. It does it all for you; all you need to do is to cut and paste. Poor spelling, grammar can risk you losing a reply


# 1 Make it easy by asking questions about their profile or even better focus on your common ground.
# 2 Be proactive and start conversations.

If you wait for others to contact, you’ll miss so many opportunities. Initiating a conversation when online dating or even out can work in your favour, especially if you are a woman. It is an excellent way to stand out because men receive much fewer messages than women.
The fact that you messaged first doesn’t mean you have to take on the masculine role of being the leader; it’s how you do it, a friendly flirtations message can open up opportunities for him to signal you’re interested and encourage him to take the lead.

As for men, women love to hear from you!

Here are the best questions to ask online dating or on your date. I recommend having at least 5 of your favourite questions that you memorise and use regularly.

They are perfect for moments when you don’t know what to say. You could set up the opportunity by saying, “I have an idea. Would you like to play a game with me?”

It’s called the getting to know your game. It saves asking the same questions of where do you live and what do you do.


  • Describe your favourite way to spend your weekend.
  • What Are Three Words That You’d Use To Best Describe Yourself?
  • Where Is Your Favorite Place In The World, And Why?
  • What Accomplishment Are You Most Proud Of?
  • What Is The Most Meaningful Thing Someone Could Do For You
  • What are you most likely to stay up all night talking about?
  • If you were a celebrity in a movie who would you be?
  • If you could build any house in the world, what would it look like?
  • What animal describes you best and why?
  • If you were a DJ, what would the soundtrack to your life consist of?
  • What would you really love to do in the next five years, if you could do anything?
  • Tell me about your first kiss!
  • What are the qualities of like in a person
  • Has any book or movie made an impact on you?
  • If you could have any career in the world, what would it be?
  • Do you have any life-changing moments?
  • Tell me about your family/ best friend.
  • Ok, what’s the craziest or most spontaneous thing you have ever done?
  • This one is super important, what is your most embarrassing moment? 😉

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